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Synthesis method of nitroazole energetic compound

A synthesis method and compound technology are applied in the synthesis field of nitrogen nitration products, which can solve problems such as lack of overall reaction mechanism, and achieve the effects of simple reaction process, good substrate universality and high yield.

Active Publication Date: 2020-06-05
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, further theoretical studies and experimental verification of its subsequent intermediates or reaction processes have not been reported, so the overall reaction mechanism still lacks strong support

Method used

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  • Synthesis method of nitroazole energetic compound
  • Synthesis method of nitroazole energetic compound
  • Synthesis method of nitroazole energetic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of N-nitropyrazole

[0031]

[0032] In a three-necked flask (25 mL) after drying in an oven equipped with a stir bar, add pyrazole (1.0 mmol, 68 mg), electrolyte n-Bu 4 NBF 4 (205mg, 0.6mmol) and ferric nitrate nonahydrate (2.0mmol, 0.808g). The three-necked flask is equipped with a graphite rod (Φ=6mm) as the anode, platinum electrode (10mm×10mm) as the cathode, and 16mL CH 3 CN, then evacuated and flushed with nitrogen as a protective gas. The reaction mixture was stirred and refluxed at a constant current of 15 mA and 70°C for 6 hours. When the reaction was completed, the reaction mixture was washed twice with water and extracted with ethyl acetate (10 mL×3). Then combine the organic layers and use Na 2 SO 4 After drying, it was concentrated in vacuo, and then passed through a flash chromatography column to obtain the pure product, which was a white powdery solid with a yield of 64%. The NMR characterization of the product was: 1 H NMR (500MHz, Chloroform-d)...

Embodiment 2

[0034] Synthesis of N-nitropyrazole

[0035]

[0036] The reaction steps are exactly the same as in Example 1, except that tetrabutylamine tetrafluoroborate is changed to tetrabutylamine perchlorate. The product is a white powdery solid with a yield of 53%. The nuclear magnetic characterization of the product is : 1 H NMR (500MHz, Chloroform-d) δ = 8.36 (d, J = 2.8, 1H), 7.66 (s, 1H), 6.55-6.48 (m, 1H). 13 C NMR (126MHz, Chloroform-d) δ=140.98, 125.24, 109.36.

Embodiment 3

[0038] Synthesis of N-nitropyrazole

[0039]

[0040] The reaction steps are exactly the same as in Example 1, except that ferric nitrate nonahydrate is changed to bismuth nitrate pentahydrate, the product is a white powdery solid, and the yield is 43%. The NMR characterization of the product is: 1 H NMR (500MHz, Chloroform-d) δ = 8.36 (d, J = 2.8, 1H), 7.66 (s, 1H), 6.55-6.48 (m, 1H). 13 C NMR (126MHz, Chloroform-d) δ=140.98, 125.24, 109.36.

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PUM

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Abstract

The invention discloses a synthesis method of an azole N-nitrated compound, and the method comprises the following steps: carrying out electrocatalytic free radical coupling reaction, and carrying outnon-oxidative nitration reaction on the N-H bond of the azole by using economic and nontoxic metal nitrate as a nitro source. According to the method, an electro-catalysis mode is adopted, various cheap metal nitrates are adopted as a nitrate source, a target product is synthesized through a one-step method, the reaction process is simple, the substrate universality is good, the yield of the generated N-nitroazole compound is high, and a green N-N single bond construction method is achieved.

Description

Technical field [0001] The invention belongs to the field of organic synthetic chemistry and relates to a method for synthesizing nitrogen nitration products of azoles. Background technique [0002] Formation of N-NO by N-nitrification 2 It is one of the most common ways to obtain N-N bonds by functionalizing N-H groups. The product N-nitroamine is a substance widely present in azo dyes and high-density energetic materials. Common energetic compounds hexanitrohexaazaisowurtzitane (CL-20), 1,3,5,7-tetra Nitro-1,3,5,7-tetraazacyclooctane (HMX) has N-NO 2 Structure, therefore, seeking effective strategies for constructing N-N bonds to prepare N-nitro compounds has become an important research topic in synthetic chemistry. [0003] The conventional mechanism of N-nitrification involves strong acidic conditions (HNO 3 ) From NO 3 - In-situ generation of nitronium ions (NO 2 + ). Then NO 2 + A two-electron transfer addition (polar addition, Ingold-Hughes method) or a single-electron tr...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 王鹏程赵季平陆明周新利
Owner NANJING UNIV OF SCI & TECH
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